121887-19-2Relevant academic research and scientific papers
Radical Reactions on N-Heterocyclic Compounds, IX. - Oxidation Reactions of Cyclic Amidrazones
Schulz, Manfred,Kluge, Ralph,Hoell, Bernd Volker,Drewelies, Juergen
, p. 1983 - 1988 (2007/10/02)
The cyclic amidrazone derivatives 1 and 2 were oxidized with dibenzoyl peroxide or bromine to give the dehydro derivatives 5 and 6, respectively.Oxidation of 2 or 6 by Fremys salt yields the quinone imine 7.Treatment of the cyclic amidrazone 3 with Ag2O afforded, via an isolable silver complex, which was decomposed by nitric acid, the 1,2-dihydro-1,2,4-triazine-5,6-dione 9 and the 1,6-dihydro-1,2,4-triazin-5(2H)-one 10.From 3 the dimer bis(1,4,5,6-tetrahydro-4-nitroso-1,2,4-triazine) 11 is formed in the usual manner.On irradiation or thermal treatment 11 yields the 1-(p-nitrophenyl) derivative 12 of 3.Photolysis of 11 in the presence of O2 leads to the hydroperoxides 13 and 14, compounds of a new peroxide type.Degradation of 13 with mineral acid leads to the unusual imido azo compound 17, reaction of 13 and 14 with bases affords the corresponding keto compounds 15 and 16. 2,5-Dihydro-1,3-diphenyl-1,2,4-triazin-6(1H)-one (4) reacts with three equivalents of the stable 2,4,6-tris-tert-butylphenoxyl radical (18) to form hippuric acid (19) and phenyldiimide (21). - Key Words: Amidrazones / 1,2,4-Triazinones / Oxidation / Azo compounds, new type of / Hydroperoxides, new type of
